Tags

Type your tag names separated by a space and hit enter

Catalytic, enantioselective, vinylogous aldol reactions.
Angew Chem Int Ed Engl. 2005 Jul 25; 44(30):4682-98.AC

Abstract

In 1935, R. C. Fuson formulated the principle of vinylogy to explain how the influence of a functional group may be felt at a distant point in the molecule when this position is connected by conjugated double-bond linkages to the group. In polar reactions, this concept allows the extension of the electrophilic or nucleophilic character of a functional group through the pi system of a carbon-carbon double bond. This vinylogous extension has been applied to the aldol reaction by employing "extended" dienol ethers derived from gamma-enolizable alpha,beta-unsaturated carbonyl compounds. Since 1994, several methods for the catalytic, enantioselective, vinylogous aldol reaction have appeared, with which varying degrees of regio- (site), enantio-, and diastereoselectivity can be attained. In this Review, the current scope and limitations of this transformation, as well as its application in natural product synthesis, are discussed.

Authors+Show Affiliations

Denmark SE
Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA. denmark@scs.uiuc.edu
Heemstra JR
No affiliation info available
Beutner GL
No affiliation info available

MeSH

AldehydesCatalysisCrystallography, X-RayEthersKetonesModels, MolecularMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Review

Language

eng

PubMed ID

15940727

Citation

Denmark, Scott E., et al. "Catalytic, Enantioselective, Vinylogous Aldol Reactions." Angewandte Chemie (International Ed. in English), vol. 44, no. 30, 2005, pp. 4682-98.
Denmark SE, Heemstra JR, Beutner GL. Catalytic, enantioselective, vinylogous aldol reactions. Angew Chem Int Ed Engl. 2005;44(30):4682-98.
Denmark, S. E., Heemstra, J. R., & Beutner, G. L. (2005). Catalytic, enantioselective, vinylogous aldol reactions. Angewandte Chemie (International Ed. in English), 44(30), 4682-98.
Denmark SE, Heemstra JR, Beutner GL. Catalytic, Enantioselective, Vinylogous Aldol Reactions. Angew Chem Int Ed Engl. 2005 Jul 25;44(30):4682-98. PubMed PMID: 15940727.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic, enantioselective, vinylogous aldol reactions. AU - Denmark,Scott E, AU - Heemstra,John R,Jr AU - Beutner,Gregory L, PY - 2005/6/9/pubmed PY - 2006/9/26/medline PY - 2005/6/9/entrez SP - 4682 EP - 98 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 44 IS - 30 N2 - In 1935, R. C. Fuson formulated the principle of vinylogy to explain how the influence of a functional group may be felt at a distant point in the molecule when this position is connected by conjugated double-bond linkages to the group. In polar reactions, this concept allows the extension of the electrophilic or nucleophilic character of a functional group through the pi system of a carbon-carbon double bond. This vinylogous extension has been applied to the aldol reaction by employing "extended" dienol ethers derived from gamma-enolizable alpha,beta-unsaturated carbonyl compounds. Since 1994, several methods for the catalytic, enantioselective, vinylogous aldol reaction have appeared, with which varying degrees of regio- (site), enantio-, and diastereoselectivity can be attained. In this Review, the current scope and limitations of this transformation, as well as its application in natural product synthesis, are discussed. SN - 1433-7851 UR - https://www.unboundmedicine.com/medline/citation/15940727/Catalytic_enantioselective_vinylogous_aldol_reactions_ DB - PRIME DP - Unbound Medicine ER -